5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Chemical Properties

Melting point:

126-128 °C(lit.)

Boiling point:

287 °C265 mm Hg(lit.)

Density 

1,12 g/cm³

vapor pressure 

0.016Pa at 20℃

refractive index 

1.6300 (estimate)

Flash point:

191°C/17mm

storage temp. 

2-8°C

solubility 

3.30g/l

pka

2.73±0.50(Predicted)

form 

Crystalline Powder

color 

Yellow to beige

PH

4.0-4.4 (H2O, 20℃)(saturated aqueous solution)

Water Solubility 

3 g/L (20 ºC)

Merck 

14,6713

BRN 

609575

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

InChIKey

QELUYTUMUWHWMC-UHFFFAOYSA-N

LogP

0.75 at 24℃

CAS DataBase Reference

89-25-8(CAS DataBase Reference)

NIST Chemistry Reference

3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-(89-25-8)

EPA Substance Registry System

1-Phenyl-3-methyl-5-pyrazolone (89-25-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

UQ9625000

TSCA 

Yes

HS Code 

29331990

Hazardous Substances Data

89-25-8(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79

MSDS

• Language:English Provider:Edaravone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Usage And Synthesis

Description

Edaravone was marketed in Japan for improving neurologic recovery following acute brain infarction. Currently, several agents classified as neuroprotectants and acting by diverse mechanisms (inhibition of glutamate release, blockade of calcium channels, lazaroids) have been marketed for treating the outcomes of brain damage due to trauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radical scavenging activity to be introduced for this pathology. This previously described molecule (in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can be simply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevone is a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edema in the brain following ischemia by blocking the arachidonic acid cascade triggering peroxidative neurodegeneration. Interestingly, this agent has been shown to quench active oxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective during reperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage.

Description

MCI-186 is a free radical scavenger with diverse protective effects in vivo. Most notably, it reduces damage due to ischemia-reperfusion injury in lung, liver, and brain in animal models of transplant, infection, traumatic brain injury, and stroke. MCI-186 provides these protective effects, at least in part, by reducing reactive oxygen species, inhibiting apoptosis, and blocking nonenzymatic peroxidation and lipoxygenase activity.

Chemical Properties

Off white to light yellow powder

Originator

Mitsubishi Pharma (Japan)

Uses

3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS.

Uses

antioxidant, lipoxygenase inhibitor

Uses

Edaravone inhibits the disease activity in rheumatoid arthritis.

Definition

ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively.

brand name

Radicut

General Description

A free radical scavenger and antioxidant that reduces post-ischemic brain injury. Inhibits iron-dependent peroxidation in rat brain homogenates (IC₅₀ = 15 μM). Inhibits mitochondrial permeability transition pore.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Not classified

Biological Activity

A radical scavenger and antioxidant which is able to protect against the effects of ischemia, probably by inhibiting the lipoxygenase system. Protects against MPTP-induced neurotoxicity.

Biochem/physiol Actions

Product does not compete with ATP.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. An eye irritant. When heated todecomposition it emits toxic fumes of NOx.

storage

Store at RT

Purification Methods

Crystallise the pyrazolone from hot H2O, EtOH or EtOH/water (1:1). It complexes with metals. [Veibel et al. Acta Chim Scand 6 1066 1952, Beilstein 24 II 9, 24 III/IV 71.]

References

1) Watanabe et al. (1994), Protective effects of MCI-186 on cerebral ischemia:possible involvement of free radical scavenging and antioxidant actions; J. Pharmacol. Exp. Ther., 268 1597 2) Yoshida et al. (2006) Neuroprotective effects of edaravone:a novel free radical scavenger in cerebrovascular injury; CNS Drug Reviews, 12 9 3) Kawasaki et al. (2007) Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one), a Radical Scavenger, Prevents 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Neurotoxicity in the Substantia Nigra but Not the Striatum; J. Pharmacol. Exp. Ther., 322 274

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one(89-25-8)Related Product Information

• PHENYL VALERATE
• Kresoxim-methyl
• Methanol
• Methyl acrylate
• Basic Violet 1
• Cefazolin sodium salt
• Methyl acetate
• Acetonitrile
• Cefazolin
• Edaravone N-Oxide
• Paraquat dichloride
• Methylparaben
• Dihydromyrcenol
• Edaravone Glucuronide
• 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
• 4,5-dihydro-a-(hydroxyMethyl)-a,3-diMethyl-5-oxo-1-phenyl-1H-Pyrazole-4-Methanesulfonic acid
• BISPYRAZOLONE
• Edaravone Impurity 26